it might just be me but when i jailbroke cydia never asked me to "make my life easier" but i think it did that by default because i somehow have blobs for 4.0.2 when i never went past 4.0.0

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Cydia automatically puts EVERYONE in a queue whenever a new firmware release comes out. It may take a few weeks until everyone gets fully processed, but as long as you've pressed that "make my life easier" button at least once in the past, Cydia will continue to cache blobs for all firmwares for your device. Very convenient, IMO.

Yup, but it can save the shsh to your computer. There is also an option to save them to Saurik's server. I think that if you do so, you will get the message in Cydia saying that it has your shsh backed up for x.x.x firmware.